methyl (3S)-3-[(2S)-2-[(2S)-2-[(2S)-2-[(2S)-2-{[(benzyloxy)carbonyl]amino}-3-methylbutanamido]-4-methoxy-4-oxobutanamido]-3-methylbutanamido]propanamido]-5-fluoro-4-oxopentanoate

• ChemBase ID: 106510
• Molecular Formular: C32H46FN5O11
• Molecular Mass: 695.7329432
• Monoisotopic Mass: 695.31778554
• SMILES: COC(=O)C[C@H](NC(=O)[C@H](C)NC(=O)[C@@H](NC(=O)[C@H](CC(=O)OC)NC(=O)[C@@H](NC(=O)OCc1ccccc1)C(C)C)C(C)C)C(=O)CF
• Canonical SMILES: COC(=O)C[C@@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)CF)CC(=O)OC)C)C(C)C)NC(=O)[C@H](C(C)C)NC(=O)OCc1ccccc1
• InChI: InChI=1S/C32H46FN5O11/c1-17(2)26(30(44)34-19(5)28(42)35-21(23(39)15-33)13-24(40)47-6)37-29(43)22(14-25(41)48-7)36-31(45)27(18(3)4)38-32(46)49-16-20-11-9-8-10-12-20/h8-12,17-19,21-22,26-27H,13-16H2,1-7H3,(H,34,44)(H,35,42)(H,36,45)(H,37,43)(H,38,46)/t19-,21-,22-,26-,27-/m0/s1
• InChIKey: ANTIWMNLIROOQF-IREHUOSBSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: methyl (3S)-3-[(2S)-2-[(2S)-2-[(2S)-2-[(2S)-2-{[(benzyloxy)carbonyl]amino}-3-methylbutanamido]-4-methoxy-4-oxobutanamido]-3-methylbutanamido]propanamido]-5-fluoro-4-oxopentanoate
• IUPAC Traditional name: methyl (3S)-3-[(2S)-2-[(2S)-2-[(2S)-2-[(2S)-2-{[(benzyloxy)carbonyl]amino}-3-methylbutanamido]-4-methoxy-4-oxobutanamido]-3-methylbutanamido]propanamido]-5-fluoro-4-oxopentanoate
• Synonyms: Z-Val-Asp(OMe)-Val-Ala-Asp(OMe)-FMK; Z-VD(OMe)VAD(OMe)-FMK; Z-Val-Asp(OMe)-Val-Ala-Asp(OMe)-Fluoromethylketone; Z-VDVAD-FMK; Z-Val-Asp(O-Me)-Val-Ala-Asp(O-Me) fluoromethyl ketone

Database IDs

• MDL Number: MFCD03452881
• PubChem SID: 162105709
• PubChem CID: 25108684

CALCULATED PROPERTIES

• Acid pKa: 11.385704
• H Acceptors: 8
• H Donor: 5
• LogD (pH = 5.5): 0.62444705
• LogD (pH = 7.4): 0.62440777
• Log P: 0.6244475
• Molar Refractivity: 168.5283 cm^3
• Polarizability: 66.56613 Å^3
• Polar Surface Area: 224.4 Å^2
• Rotatable Bonds: 22
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: DMSO/DMF: soluble20 mM
• Apperance: white powder

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: -20°C

Pharmacology Properties

• Gene Information: human ... CASP2(835)mouse ... CASP2(12366)rat ... CASP2(64314)

Product Information

• Purity: ≥90% (TLC)
• Shipped in: dry ice
• Linear Formula: C32H46N5O11F

DETAILS

MP Biomedicals - 03FK016

A cell-permeable and irreversible inhibitor of caspase-2 (ICH-1)

Sigma Aldrich - C1605

Amino Acid Sequence
Z-Val-Asp-OMe-Val-Ala-Asp-OMe-FMK
Biochem/physiol Actions
A cell-permeable inhibitor of caspase-2, which exhibits competitive and irreversible inhibition.

REFERENCES

• Zhuang, S. et al., Am. J. Physiol. Cell. Physiol., 279(2):C341 (2000).
• Talanian, R.V. et al., J. Biol. Chem., 272(15):9677 (1997).
• Gregoli, P.A., and Bondurant, M.C. 1999. J. Cell Physiol. 178, 133.
• Thornberry, N.A., and Lazebnik, Y. 1998. Science 281, 1312.